As we have moved firmly into the 21st century and as our society and its expectations are continuously evolving, so must our higher education advancement practices. Rather than asking How do we want alumni and donors to engage with our universities?, we must ask How are these individuals already intuitively engaging the world? Instead of falling into the trap of thinking What are global best practices in higher education advancement?, we should be asking Which global companies are curious and responsive in their interaction with humans, and what can we learn from them? In answering these questions, this thesis tests a human-centered solicitation approach via three primary channels: mail, phone, and email. For each channel, multiple tests were performed and the principles and tools of human-centered design and user experience are implemented, including ethnographic interviews, user personas, and A/B testing. The results of these tests lead to the recommendation of a user-centered approach to philanthropic interactions that is constantly testing and evolving practices. Now more than ever, consciously building and testing systems centered around removing obstacles impeding giving defines the work of the modern advancement professional.